1-Bromo-2-butanone → Benzyl 2-amino-4-ethyl-1H-imidazol-1-carboxylate

HRID 1160464Notes

Reaction equation

HRID 1160464 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([NH2:14])=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:25][C:26](=O)[CH2:27][CH3:28]>C(OCC)(=O)C>[NH2:13][C:12]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:25]=[C:26]([CH2:27][CH3:28])[N:14]=1

Participants

5

Reactant 3

HCID 131561-Bromo-2-butanoneHCID 81531DiisopropylethylamineHCID 178513108HCID 178513108, compound

Product 1

HCID 57815117Benzyl 2-amino-4-ethyl-1H-imidazol-1-carboxylateYield 33.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzyloxycarbonyl guanidine 2.52 g (13.1 mmol), diisopropylethylamine 1.81 ml (8.7 mmol), 1-bromo-2-butanone 0.89 ml (8.7 mmol) and ethyl acetate 50 ml was stirred at room temperature overnight. The reaction solution was washed with water and aqueous sodium chloride solution and dried on magnesium sulfate. After evaporation of the solvent, the residue was purified by a column chromatography on silica gel and further recrystallized from n-hexane to give 0.71 g of the title compound (yield: 33%).

Workup

  1. washThe reaction solution was washed with water and aqueous sodium chloride solution
  2. customdried on magnesium sulfate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by a column chromatography on silica gel
  5. customfurther recrystallized from n-hexane

Sources & evidence

ORD record
ord-46ab8474370845d59bbafb205aaa4c1e
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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